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4. Wally Cleaver

Show (Air Dates): Leave It to Beaver (1957-1963)Actor: Tony Dow

Inspired by Don Draper's style? Try going to the source: Wally Beaver, the much-beloved character who documented the drool-worthy wares from the late '50s and early '60s while they were still being worn. Everything Wally donned—from short-sleeve plaids and slim polos to streamlined suits and skinny ties—is still the epitome of casual cool. And when it came to snagging the ladies, his baby blues didn't hurt either.